


The Professional Stretcher

by SoraJinsei



Series: NSFW [1]
Category: Supernatural
Genre: Aftercare, Anal Fingering, Anal Gaping, Anal Play, Anal Plug, Anal Probing, Anal Sex, Attraction, Bottom Dean Winchester, Butt Plugs, Castiel/Dean Winchester Mutual Pining, Dean is a male escort, Dom/sub, Humor, Light BDSM, M/M, Manhandling, Mutual Pining, Porn With Plot, Rimming, Sex Toys, Sexual Content, Smut, Spanking, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2019-10-21
Updated: 2020-08-25
Packaged: 2020-12-27 07:42:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 5,988
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21115181
Author URL: https://archiveofourown.org/users/SoraJinsei/pseuds/SoraJinsei
Summary: Dean's a popular Male Escort. He doesn't exactly have time to prep himself for his dates, that's why he calls in the professionals to help him get ready.





	1. Chapter 1

  
  
  
Cas glanced down at his watch as he rode the elevator up to the top floor always dressed casually in his jeans and a loose t-shirt with his mandatory black bag in one hand.  
  
Always punctual.  
  
The elevator dinged before opening and leading him into a long hallway. The room he was looking for was at the end.  
  
The man he was here for was not exactly a regular but he calls often enough that he may just become one.  
  
From what Cas knows of the man, the guys got quite an extensive customer list. He was already really popular with the ladies. His male clientele has been slowly growing from what they've discussed during these last couple of sessions.  
  
Castiel stopped at the door, raising his hand to knock.  
  
It didn't take long for the door to swing open, revealing a handsome man with nothing on but gray sweats, his lightly tanned skinned torso with freckles everywhere, sandy brown hair and the greenest eyes Castiel has ever seen.  
  
"Hello, Dean,"  
  
"Hey Cas, right on time," Dean quipped, holding a hand out, gesturing for Castiel to come in.  
  
After shutting the door, Castiel took in the familiar settings of the apartment. A kitchen set right next to the doorway, the spacious living room before him with a dining room off to the left. The hallway next to the kitchen leading down to the bedroom and bathroom.  
  
"Who is the client today," Castiel questioned as he turned to look towards Dean who was cleaning up the kitchen.  
  
Humming to himself, Dean placed the rag he was using into the sink as he came around the counter to join Cas in the living room.  
  
"He's new, some big corporate bigwig needing some stress relief," Castiel nodded along in understanding. Those secretly gay types. Probably has that apple pie life with a wife, 2.5 kids, white picket fence and dog to boot.  
  
"I see why you'd need me then," already picturing how rough this guy will be. "The couch, as usual?"   
  
Before Castiel made his way to the familiar chocolate loveseat, he heard a low cough, stopping him in his tracks.  
  
"Actually, I was wondering if we could do this in the bedroom?"  
  
Raising a brow at the question, Castiel nodded his head as he was lead down the hall. When Dean first started using their services, Castiel had remembered the man asking if they could use the bedroom.  
  
The more comfortable he got, the less he cared about where he was being prepped.  
  
The room was simple, a queen size bed with a comfortable-looking blue comforter. A lot of fluffy pillows at one end. One nightstand, a dresser, a closest off to the right with an attached bathroom next to it. Pretty plain based on the rooms Castiel has seen since working for the company.  
  
“Have you eaten anything today?” Castiel questioned, starting their usual routine of questions. He turned in time to see Dean pushing down his sweats so they’d pool at his ankles. For a man of his size and structure, he was very well hung. No wonder his female clientele list was long.   
  
“Just water. I ate last night though,”  
  
“Bowel movements?”  
  
“Yes, about an hour ago. I’m all clean, took a shower and everything,” Nodding his head, Castiel walked over to the bed to place his black bag on it.  
  
“Well let’s get started. When are you meeting this guy?” Castiel asked as he watched Dean crawl onto the bed. He moved back on his hands and knees so his knees were inches away from the edge, before dropping to his forearms to present his ass towards Castiel.  
  
_“And what a pleasantly plump ass it was.”_ Castiel thought as he opened his bag that was next to Dean to pull out the lube and black latex gloves.  
  
“In an hour or so, or whenever his business meeting ends. Everyone is supposed to be leaving for lunch today,”  
  
“So you’re having an office fuck. You haven’t had one of those before,” Castiel commented as he pulled the gloves on and moving to place himself directly behind Dean “How are you feeling?” while placing a hand on man’s ass, the other grabbing the lube.  
  
“I’m feeling awesome,” He watched Dean look over his shoulder to wink at him. Castiel rolled his eyes at the comment. “Fine,” in an exaggerated voice. “Everything is good, but I’d feel comfortable going slow today.”  
  
Nodding his head in understanding, Castiel popped the lube cap open and pouring some onto his gloved finger. He rubbed it between his thumb and two fingers to warm it up before placing it at the entrance of the awaiting hole before him.  
  
Slowly he pushed his middle finger in without any resistance. He started slow, in and out, hearing the slight hiss from Dean every now and then. It didn't take long for Castiel to add the second digit.  
  
He pushed the two fingers in, all the way to his knuckles, keeping them there to allow Dean to adjust.  
  
A low moan from the man below signaled that he was getting used to it.  
  
Keeping his two fingers still deep in Dean, his other hand reached into his bag, digging around until his hand felt the cool touch of steel of the item he was looking for.  
  
"How big is this guy?" Castiel questioned, wiggling his fingers around before starting to pull his fingers in and out.  
  
Dean grunted out, letting his head falling between his arms.  
  
"From what I was told," he panted out, "He's bigger than me," Castiel nodded at the information, deciding that Dean was good by pulling his fingers out.  
  
Dean shuddered, his ass leaning back at the loss of contact. Castiel couldn’t help but stare at it. Perfectly round, plump, definitely chiseled from the finest piece of rock known to man. What Castiel wouldn’t give to see it gleaming red from being spanked by his hand.  
  
_“Breath,”_ Castiel thought to himself. Remembering the rules set by his company.  
  
They came to assist in stretching the Male Clients before their Scene or their “Dates”. Giving in to the moment like this could garner a bad reputation for them. Even though this is the only company that does this, positive feedback is what keeps them in business.  
  
“So much for going slow,” Dean commented, glancing over his shoulder and seeing the plug in Castiel’s hand.  
  
“You adjusted quickly. Besides, we’re already ten minutes in,” Castiel replied, uncapping the lube again, squirting a generous amount onto the metal plug. “And you always have trouble with this part,” he rubbed his gloved hand over it, trying to warm it the best he could.  
  
“What can I say? You have gentle hands,” Castiel looked down at the man, the tip of the plug already placed at the puckering hole, slowly pushing it in. "Except for that" Dean ground out, head falling back between his arms.  
  
And this was the smallest one Castiel had.  
  
Watching the small silver plug inch it's way deeper into the man, Castiel had to look away.  
  
"S-slow," Dean uttered out under his breath.  
  
And Castiel did. Slowly pulling the plug out and pushing it back in. Dean’s head lifted, followed by the rest of his torso so that he was on all fours.  
  
In doing so gave Castiel a clear view of the hard, weeping cock Dean was sporting.  
  
“You’re good,” Dean commented after taking a deep breath.  
  
Castiel gripped the plug again, pulling it completely out. He stared at the puckering hole once again as he placed the used item on the towel he just produced from his bag.  
  
With his clean hand, the one without lube on it, he opened his bag by the handle to look at his options.  
  
“Is he bigger by length or girth?” Castiel questioned, staring at what he had.  
  
“I don’t know,” Dean glanced over his shoulder at Castiel. “Girth probably.”  
  
Choosing the next item, he lathered it extensively. This is as big as anyone could get so it should be good.  
  
“Move up,” Castiel ordered, watching Dean move farther up on the bed. Shifting out of his shoes, Castiel moved onto the bed as well, one knee between Dean’s legs and the other on the outside. Placing one hand on Dean’s lower back, he placed the instrument at the entrance.  
  
“Take a deep breath and relax,” Castiel warned as he added pressure to get the item past the ring of muscle. He heard Dean grunt at the intrusion, panting a little as he fought to control his breathing.  
  
“Dean,” How long has it been since their last session? Probably two weeks ago? Shaking his head, he pulled the item back and then pushing it in a little more. He was met with little resistance after each thrust. He was getting used to it. Good.  
  
Castiel had just managed to get the toy up the hilt when he heard a strangled noise. He paused.  
  
“Stop,” Dean forced out, dropping to his elbows, forehead resting on the bed.  
  
Castiel looked down, hand seizing its movement of pulling out. He let go of the flat hilt part, his eyes glancing down towards the man's feet. His toes are curled tight, looking around, the hands were clenched as well.  
  
That's when he noticed the problem. There was an obvious stain from all the precum dripping from the man's weeping cock, straining hard from lack of contact.  
  
Stuff like this does happen. The easiest way is to either help them relax or stop until the problem relieves itself.  
  
"J-just give me a moment," Dean said, a little breathless, one of his hands coming up to cover his face.  
  
“Would you like my assistance?” Castiel asked, a little taken aback at the situation. He’s been assisting Dean for the past year and a half and never has this happened with him before. Generally, it’s been casual, simple and downright friendly.  
  
Dean always keeping the situation light between them with jokes and entertaining stories. But this was different.  
  
“Dean,” Castiel asked again.  
  
“P-please,” the man managed out, completely out of character for Dean.  
  
Castiel starred. He’s done this before. Both professionally and to the other men, he’s been with personally. But this was Dean.  
  
Taking a moment to compose himself at the new scenario, he slipped

back into 'professional' mode as he moved closer.  
  
Reaching down for the lube, he uncapped it and squirt a generous amount into his hand. Tossing the bottle back into his bag, he took the mans’ length in his left hand, swiping his thumb over the slit to smear the precum there and moved his hand around the length to smear the lube.  
  
Hearing Dean whimper at the contact right as Castiel started his slow strokes along his length, allowed him to use his right to slowly pull the toy out again.  
  
Having someone ejaculate during these sessions is not uncommon. Like Castiel thought earlier, he’s had to do it professionally before. It’s one thing to see Dean’s dick, but to have it in his hand now. Castiel had to work on his breathing, trying not to get caught up in the moment. He kept his focus on the matter at hand, eventually getting the toy in sync with the stroking of Dean’s length.  
  
The man’s breathing became ragged, whimpering from the assault, as he got up on his hands so that he was on all fours, again, so that he could start pushing back into the toy and forward into Castiel’s hand.  
  
It didn’t take long.  
  
Dean bit his lip, muffling a cry as he came all over Castiel’s hand and comforter, his body shuddering through his orgasm.  
  
Hands freezing in place as the man before him slowly dropped to his elbows, Castiel could see the man’s torso expanding and collapsing as Dean tried to regain his breathing.  
  
It was quiet.  
  
Neither one speaking. Of course, what could Castiel say in a situation like this...  
  
“Y-you can...you can take it out,” Dean ground out, turning his head to peer at Castiel.  
  
Without a word, Castiel grabbed the hilt of the toy and slowly pulled it out. Dean grunting at the feeling, groaning once it was completely out.  
  
Placing the toy with the plug on the towel, he folded the cloth over them nicely before placing the bundle into his bag.  
  
Removing the gloves, turning them inside out, he walked into the attached bathroom to dispose of them into the trash. When he walked out, Dean was completely stretched out flat on his bed, his head buried into his pillow.  
  
“Make sure to drink plenty of water,” Castiel commented, walking back to his bag that was next to Dean.  
  
A grunt was his only response.  
  
“Do I need to stay to make sure you’re ok?” Castiel questioned, watching the man not move.  
  
His response was Dean lifting his arm to wave at him.  
  
Taking his cue to exit, Castiel grabbed his bag and headed for the bedroom door.  
  
It wasn’t until he got to the front door, Castiel’s hand keeping it open so he could lock it behind him, as he was grateful that Dean hadn’t seen the bulge that Castiel was sporting from the noises and the beautiful view of the man cumming had done to him.  
  
Never had he had a client affect him the way Dean did just then?


	2. Chapter 2

Dean stared up at the dark ceiling, watching the dark outline of the ceiling blade fans as his current date curled against his side with one leg hooked around his. She was becoming a new regular, hiring him for parties at work, events, and just recently her 10-year high school reunion. That one had been interesting.

He sighed, one arm wrapped around the girl, her head nestled on his bicep. His other hand moving to rest behind his head.

Try as he might, he couldn't sleep.

His mind wandering around his thoughts until he came to a particular day. A couple of weeks ago to be exact.

He remembers lying in utter bliss on his bed after having just finished his stretch session with Cas. Dean was equal parts happy and embarrassed about what happened.

Happy because he finally got the amazingly good looking Professional Stretcher to jerk him off.

Embarrassed because he wasn't able to hold back, cumming quicker than when he was first discovering his body.

But overall, he was stuck on an emotion he couldn't quite pinpoint.

He'd been secretly crushing on this guy since the first day they met. Sure that's a loaded statement, considering he's been using the Professional Stretchers shortly after he decided to open himself up to male clients.

His first encounter with a male client had resulted in some serious pain. Even though the guy had apologized profusely, despite being gentle as hell, it still hurt.

After that, someone had given him information on people that can help him prep for stuff like this. It was weird at first, but in the long run, it helped out a lot.

But the first couple of guys who helped him, one had been a real asshole. Another, geez, it was his first day! Don't get him started on the one was hitting on him right in the middle of prepping, went to touch Dean without his permission. His excuse was that he thought Dean would have been 'ok' with it.

And you bet your ass Dean reported each one until he got Castiel.

Cas, Dean had nicknamed him.

When Castiel came in, the guy was the total Professional that he was supposed to be. Kept the talking to a minimal, did his job with precision because he knew what he was doing and the guy was really gentle.

Dean's thoughts changed direction on him. Back to the night, he was supposed to meet that office bigwig. The guy had been such an asshole.

After Dean had walked into the office, he noticed the guy was buff as hell, his suit barely containing the rippling muscles underneath.

The man stood at Dean entering the room, walking around the desk to greet him.

With new clients, Escorts are supposed to sit down and discuss what is allowed and what isn’t, who is comfortable with what. And so forth. Trying to establish a connection so to speak.

But this man had walked right up to Dean, undid his pants, and whipped his dick right out.

No foreplay, no nothing.

When Dean said no, the bigwig had gotten angry, started calling Dean a high-end prostitute and to suck his dick like the good little fag that he was.

In return, Dean did the only thing he could think of.

He punched the man in the Dick.

After the guy keeled over in pain, Dean exited quickly.

Bursting through his doors, Dean was such a pissed off mood that he told Meg to tell his clients that he was busy for however long and that later he would send a gift basket or flowers, or something as an apology.

He also told her to blacklist that client, explaining in detail what the man had done.

Dean shook his mind of the rest of the night and the ones after as the girl next to him cuddled closer.

He glanced down at the peaceful look, his mind going back to the way Castiel had gripped him, not too hard, but enough to give that feeling of tightness to help him along.

The way Castiel stroked him in tandem with the thrusts of the toy to leaving his hand still, making Dean thrust forward and back for the friction while impaling himself with the toy.

A hum beside him disrupted his thoughts, Dean looked down to see the girl looking up at him sleepy eyes, a small smile pulling at her lips.

"Round two already?" She whispered, her gaze turning downwards to the clear erection he was sporting. She looked back at him, a smirk replacing the smile as she maneuvered herself up and onto his lap.

"You're paying extra, so why not?" He commented, placing both hands on her hips as she slowly slid herself along his length.

-

Dean threw his phone across the couch, an irritated sigh at the news he had just received.

Cas wasn't available.

That's the third time in a month the guy has been unavailable. The girl on the line had told him that Castiel had gone on vacation for two of those weeks while taking personal time off. After coming back, his schedule became booked real quick.

He knew Cas was good. Probably the best. But to be booked up to 2 months in advance, that's just downright insane. Who has dates that far in advance for Ass Stretching?!

But did Dean book an appointment, he may have. He should have a male client around that time.

So what did Dean do in those two months of waiting?

He continued with his female clientele, only meeting with the male clients if they were the ones that just wanted companionship.

As for the ones who wanted sex, he had to make up an excuse over the phone as to why he couldn't do anything. One guy got so concerned that he thought Dean got some kind of butt crab infection. Whatever that is.

After the long and antagonizing two months, he received a text from the company that Castiel will be arriving at Dean's apartment tomorrow at 2 pm.

Did Dean jump up and down in joy?  
You bet your sweet ass he did.

Will be ever tell a soul he did it?  
Possibly his friend Charlie, but no one else.

He was grinning like a fool when day turned to night then back to the morning.

He had an hour left until the man's arrival when something burst his bubble.

What if Castiel didn't feel the same?

Dean brought his hands to grip hair, how could he be so stupid to forget such a huge detail?

The only reason Castiel helped jerk Dean off was that Dean had asked him and it was part of his job to help ease the process.

But then the way Cas had looked at Dean popped in his head.

That gentle expression as his features softened as if he was admiring Dean's physique.

Mixed signals. Wires crossing. Brain function overload.

Pacing back and forth, arguing with himself in his head, he almost missed the knock on his door.

Stopping suddenly, his entire body acting as if it had been dunked in an ice bath, he stayed where he was. Maybe if he didn't move, they won't knock again?

"Dean?" Another knock.

Castiel.

Gulping, his throat suddenly dry, he looked down at himself. Maybe he should have worn a shirt? Too late now, taking in his black sweat pants.

He got to the door right at the third knock, opening it in time to see Castiel's hand still in the air.

"Hello, Dean," he greeted in that deep gravelly voice.

"Cas," Dean answered, a little breathless. No idea why. Probably because his heart was racing.

"Sorry about the prolonged appointment," he commented, referring to the wait time for his services.

"It's ok, I'm just surprised that you managed to have a waitlist of two months. I've only had that happen a handful of times for me,"

Crap, he's bragging. That's such a narcissistic thing to say. This could ruin things.

Castiel chuckled, that's when Dean realized they were still talking in the doorway. He opened the door wider to let the man in, taking in his appearance.

A blue business suit under a tan trench coat. Wonder where he just came from?

"I'm not surprised. You of all people would have a long clientele list," a compliment that went straight to Dean's heart. "Who's the special client today?"

Another strike. Does Cas keep tabs on Dean's client? I mean, it wouldn't be unusual. Thinking about it now, they do discuss the ones he's been with during their sessions.

"Uh, Aaron," he lied.

Castiel looked over with a raised brow.

"Correct me if I'm wrong, but aren't you the one that does him?"

Crap.

"Yeah," Dean's voice raising slightly at the lie. "He told me he wanted to experiment by switching roles,"

Castiel stared at him. It took a lot for Dean not to flinch or twitch under that gaze.

"It's not exactly unheard of," Castiel said, breaking the silence. "Are we using the bedroom again?" He questioned, shifting himself so that he was holding his black bag with both hands.

Wracking his brain, would it be too obvious to do it in the bedroom again? Or would the couch throw off the scent? Even though the bedroom had been really comfortable. But the couch would give the perfect angle if this went any further.

"Couch," if Cas cared, either way, he didn't show it as he turned in the direction of the loveseat.

Dean watched as Cas placed his black bag on the coffee table, reaching in for those black latex gloves and lube.

After taking off the ridiculous trench coat and suit jacket, he watched Castiel roll up his sleeves, which makes any man 5,000% hotter.

Snapping the gloves into place, Castiel turned his attention to Dean with a raised brow.

"Everything ok, Dean?" He asked casually like this is an everyday thing. Which it is, to him at least.

"Yeah, fine,"

Cas stared at him for a second, his eyes squinting a bit as his head cocked to the side. Like he was analyzing Dean.

“So...shall we start?” Indicating to the empty spot he was expecting Dean to be occupying. Making an ‘oh’ face, Dean made his way to the loveseat, taking a moment to compose himself before dropping his pants. Cas didn’t even give him a second look as he was squirting lube on his two-fingers. He did look up expectantly as he rubbed the liquid between his fingers to warm up the lube.

Taking that as his cue, he crawled onto the loveseat to present his ass. It didn’t take too long to feel that firm, callused hand hold his hip as he felt a finger slowly push in.

“You’re much tighter than usual,” Good thing Cas couldn’t see Dean’s face, it’s probably as red as a tomato. “When was the last time you had any prepping done?”

A couple of thrusts from that finger and few deeps breaths later, Dean was able to answer.

“Not since the last time you were here,”

The finger stopped.

“I-I apologize if it’s because you were waiting on me-”

“No,” Dean said a little too quickly. “Just after that night, I took a break.”

It was quiet. Cas’ finger still in his ass but not moving.

“You took almost a two-month break...did something happen with that office client?” Was that concern and irritation in Cas’ voice? Dean was hesitant at first, reluctantly revealing what had happened from the time Castiel left to now.

It was quiet again and Dean didn’t like that.

“I’m sorry, Dean,” Cas said abruptly, the finger starting its slow thrusts again. “If it makes you feel any better, I don’t see you as a ‘high-end prostitute’”

“Gee, thanks,” Dean commented sarcastically.

“What I mean is, Escorts are supposed to keep people company. They are selected for their warmth, appearance, intelligence, humor, and charm,” Dean could feel his cheeks heating up at the compliment. “I believe sex is just a bonus because when you find someone you can make a connection with, sometimes it feels right and sometimes it’s not.”

The note of sadness at the end caused Dean to look over his shoulder at the man who happened to look up from what he was doing. Their eyes locked. Such an intense gaze.

“Uh, Cas, the last person who looked at me like that...I got laid,” An attempt at humor at a time like this, Dean needed to work on his timing. In response, a second finger was added, causing Dean to lose his train of thought, moaning at the intrusion.

"By proxy, you are 'getting laid'," Cas countered.

"Toy's don't count,"

"Only if you don't climax,"

"Aw Cas, are you offering your services to help me again?"

"If it'd help the process along for you, I'd be happy to oblige"

Dean's head dropped onto his folded arms, face heating up again. Happy to oblige.

"Then can I make a request then?"

The fingers stopped.

"A request?" The question hanging in the air like a thick fog. And when Dean didn't answer right away, those fingers disappeared, a sliver of dread drifted through his mind.

When Dean looked over his shoulder to see the expectant look from Cas, he internally groaned. He started this slippery (no pun intended with lube still in his ass) slope, might as well fall all the way down.

He turned around until he was able to sit on his legs, so his ass wasn't touching the couch, in front of the man.

Castiel still giving him the look.

"I-well-I wanted to know what other services do you…" letting the question hang as Dean's eyes drifted towards Castiel crotch.

Realization seemed to smack Cas hard in the face when his eyes widened.

"Dean,” his voice stern, peering down at Dean as he turned his body to reach for his bag.

“Please,” it came out softer then Dean intended, his hand reaching out for the man’s wrist to stop him from whatever he was going to do, while his other hand, with a slight tremble, placed itself on the man’s crotch. A jolt of satisfaction spread throughout Dean when he could feel the slightly hardening dick beneath the cloth.

Glancing up at the man through his lashes, the man’s jaw was tense, head straight but his downward gaze was focused completely on Dean.

So Dean continued, letting go of Cas’ arm to unbuckle the belt.

Unzipping the pants.

Dean’s heart pounding in his ears after placing one hand at Cas' hip to bring him closer.

Relieved that he wasn't met with resistance.

He reached through the hole in the man's briefs with the other hand to pull out his prize and holy mother of everything good.

From behind two layers of fabric, it did no justice for the sheer size of this man.

Cas' dick popped right out from its restraints, mere inches from his face. Dean turned his gaze upwards to the man before giving the head a small lick.

He was rewarded with a hiss in response.

Taking that as his cue, he took the tip of it to his lips and giving it a slow suck.

Dean hadn't realized he'd closed his eyes as he swirled his tongue around the slit or when he felt a hand on the back of his head.

Opening his mouth and relaxing his jaw, he kept his head still as he felt the Cas' dick slowly slide past his lips, his teeth, his tongue till it hit the back of his throat.

Lucky for him, he doesn't exactly have a gag reflex anymore.

Cas slide himself out before pushing back in just as quickly. The moan that came from the man's lips was so deep and sexy sounding that Dean was lucky he didn’t cum right then and there. Cas thrusted roughly back into Dean's mouth however many more times before letting go of Dean's head.

As gross as it is, Dean didn't mind the excess spit that comes with a rough face fuck.

"Turn around," Cas demanded, voice deep but sounding completely wrecked.

Dean had just managed to get his heart to calm down only for it to jump right back up to a heart attack.

He did as he was told, after watching Cas remove the latex gloves, his knees spread apart with his arms and head resting on the backrest.

He expected to hear the uncapping of lube, instead, he felt something wet around the rim of his hole.

_'F-fuck! He's using his tongue'_ Dean thought to himself, groaning at the feeling, trying to push back at the sensation. Two strong hands on either side of his ass kept him still, kneading the meat there just before he felt that tongue push past the ring of muscle.

Moaning at the feeling of the tongue pushing as far as possible, Dean let his head drop past his arms, letting out a string of moans and curses at how amazing it felt.

Through the long pleasure (torture) of just his tongue, Cas added a finger then two, all the while lavishing Dean's hole with that sinful tongue.

Dean was so caught up in the pleasure wrecking throughout his body that he didn't hear the uncapping sound of lube or both hands disappearing from his ass.

It was when Cas' tongue disappeared and a very manly whimper escaped Dean's lips did he look over his shoulder.

"Now now," Cas drawled out as Dean watch him reach into his bag. “Can’t have this session end too quickly,”

Glaring at the man for bringing up their last session, it quickly vanished when he watched Cas pull out a butt plug. It was bigger than the previous ones he’s used but smaller than Cas’ actual size. Dean watched as he lathered it up before turning in his direction.

Breath hitching at the intrusion, Cas’ hand on his shoulder while the other easily guided the plug, he tried to relax his breathing as he felt it inch its way inside.

Hearing the hum of satisfaction once the plug was all the way in, Dean yelped when those hands gripped his body to manhandle in to lay long ways on the couch.

Before Dean could think of how much he enjoyed the sensation of being manhandled, the stinging in his as completely distracted him.

“Fuck!” He cursed out, hands on the armrest with his head laying on the cushion, ass sticking out in the air for another smack.

Another hard smack had Dean biting his lip, the stinging and the plug still in his ass, swiftly followed by three more smacks to either cheek.

“Punishment, for glaring.” Another two smacks.

Dean had lost track of how many he received, his cheeks must tomato red at this point when he didn’t receive another, his body tensed. Maybe this is just to build anticipation?

He felt fingers grasp the flat surface of the plug and a slight tugging. He shuddered at the empty feeling combined with the pain of his ass.

“So beautiful,” he heard Cas utter under his breath, hearing the squirt of the lube bottle. Glancing over his shoulder, Dean groaned at the sight of Cas’ applying a generous amount of lube to his thick cock.

Dean watched and felt Cas place a hand on his hip as he guided his cock to Dean's hole. Gripping the armrest, the feeling of his cock was much bigger than the plug.

“F-fuck,” Dean moan out, as Cas started to slowly rock himself, inching deeper with each thrust. Only when he felt that Cas’ was fully sheathed, the feeling of the man's sharp hip bones against his bruised ass and the deep groaning sound did Dean let himself breath.

Deep breath in. Deep breath out. And Repeat.

“All that prep and still so tight,” Castiel murmured, pulling out before slamming back in causing Dean to let out a strangled yelp.

Thrusting again right before speeding himself up to a bruising pace. Dean felt the man gripped his hips tightly, pushing Dean into the cushions with every thrust.

Dean, gripping the armrest for dear life, stuck in the position. Not that he was complaining. Moaning loudly when he hit a particular spot over and over.

“I-I-” was all Dean could get out, his muscles tightening as he came. Untouched.

That only seemed to encourage Cas to go faster, his hips stuttering not too long after. Feeling that dick throb in his ass would make Dean cum again if the pain from his ass wasn’t settling in.

There was silence except for the heaving breathing between the two. It was like time froze, the two stuck in that position. Who was gonna move first?

Turned out to be Cas, because Dean was not gonna move. He felt Cas slowly pull out, whimpering in a manly way, when he felt that dick slide out completely, followed by a satisfied groan from the man above him.

Dean lay there, ass still in the air. Not a care in the world as he revealed in post-orgasmic bliss. He didn’t hear the noise in the kitchen or ruffling through drawers. He did hear the light footfalls coming closer and that deep gravelly voice telling him he should move to the bigger couch.

Dean groaned in protest.

“Dean,” Cas commanded in that deep, just had sex, voice.

“Fine,” he complained, slowly righting himself up. Pain radiating from his ass.

He walked to the couch with the assistance of Cas' arm on his lower back. Guiding him to lay on his stomach. Dean nearly jumped out of his skin when he felt cold touch his ass.

“A little warning,” Dean complained, hands gripping into fists, head sinking into the cool cushion.

“Sorry,” Cas apologized, one hand holding both ice packs to the mans’ asscheeks.

Then it was quiet. Neither one saying a word.

But Dean did pop his head up and turn it towards Cas, who was sitting on the floor next to him, in time to make eye contact with him.

Dean was the first to smile, Castiel following suit with his own.

No words were needed to be said as Dean unfolded the arm closest to Cas.

Placing his hand on the back on the man’s neck.

With little encouragement, Cas went with it until the two met in the middle for a long kiss.

**Notes for the Chapter:**

> Hope everyone enjoyed this :D
> 
> Please comment below and leave kudos!


	3. Art!

**Notes for the Chapter:**

> I had the Lovely and Extremely talented "The Friendly Pigeon" commission this amazing piece of art ^.^
> 
> http://thefriendlypigeon.tumblr.com


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